#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:52:29 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179676 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/28/4512842.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4512842
loop_
_publ_author_name
'Martin, Adam D.'
'Britton, Joshua'
'Easun, Timothy L.'
'Blake, Alexander J.'
'Lewis, William'
'Schröder, Martin'
_publ_section_title
;
 Hirshfeld Surface Investigation of Structure-Directing Interactions
 within Dipicolinic Acid Derivatives.
;
_journal_issue                   4
_journal_name_full               'Crystal growth & design'
_journal_page_first              1697
_journal_page_last               1706
_journal_paper_doi               10.1021/cg5016934
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C28 H28 N2 O8'
_chemical_formula_sum            'C28 H28 N2 O8'
_chemical_formula_weight         520.52
_chemical_name_systematic
'?tetraethyl 4,4'-(1,4-phenylene)bis(pyridine-2,6-dicarboxylate)'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-08-21
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                113.673(7)
_cell_angle_beta                 92.345(6)
_cell_angle_gamma                107.500(6)
_cell_formula_units_Z            1
_cell_length_a                   6.7914(4)
_cell_length_b                   10.0137(7)
_cell_length_c                   10.9532(10)
_cell_measurement_reflns_used    2279
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.45
_cell_measurement_theta_min      4.49
_cell_volume                     639.40(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 0.9948
_diffrn_measured_fraction_theta_max 0.9572
_diffrn_measurement_details
;
  1 omega  -50.00   33.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000 -150.0000 83

  2 omega   -2.00   34.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   30.0000  -60.0000 36

  3 omega -107.00  -14.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000   60.0000 93

  4 omega  -46.00  -16.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   30.0000  -60.0000 30

  5 omega  -91.00   -2.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000  -90.0000 89

  6 omega   37.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.6627 -125.0000 -180.0000 28

  7 omega   36.00   62.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000    0.0000 26

  8 omega   47.00   77.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000 -180.0000 30

  9 omega   34.00   68.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000    0.0000 34

 10 omega   45.00  112.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000 -120.0000 67

 11 omega   47.00   84.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000  -90.0000 37

 12 omega   36.00   98.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  -60.0000 62

 13 omega   28.00  146.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -15.0000   30.0000 118

 14 omega   41.00  120.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -61.0000   60.0000 79

 15 omega   75.00  118.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000    0.0000 43

 16 omega   63.00  103.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000   30.0000 40

 17 omega   48.00   83.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000 -150.0000 35

 18 omega   66.00   91.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000 -120.0000 25

 19 omega  110.00  174.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   77.0000    0.0000 64
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0090878000
_diffrn_orient_matrix_UB_12      -0.0396269000
_diffrn_orient_matrix_UB_13      -0.1518137000
_diffrn_orient_matrix_UB_21      0.2308312000
_diffrn_orient_matrix_UB_22      0.0089630000
_diffrn_orient_matrix_UB_23      0.0135600000
_diffrn_orient_matrix_UB_31      -0.0721968000
_diffrn_orient_matrix_UB_32      -0.1744086000
_diffrn_orient_matrix_UB_33      -0.0344904000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4245
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.277
_diffrn_reflns_theta_min         4.485
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             274
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.1051
_exptl_crystal_size_min          0.0552
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.24
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0508P)²+0.1671P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                2253
_reflns_number_total             2503
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5016934_si_001.cif
_cod_data_source_block           oadmlc_compound_5
_cod_depositor_comments
;Adding full bibliography for 4512838--4512843.cif.

 Adding full bibliography for 4512838--4512843.cif.
;
_cod_original_cell_volume        639.40(9)
_cod_database_code               4512842
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         'C28 H28 O8 N2'
_chemical_oxdiff_usercomment
'OADMLC #12577 LIGHT FOMBLIN ON MICROMOUNT FOR ADM/MS'
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C8(H8), C1(H1)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C12(H12A,H12B,H12C)
;
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O3 O 0.20907(13) 0.13132(10) 0.27830(8) 0.0217(2) Uani 1 1 d . .
O2 O 0.44305(15) 0.34788(10) 0.75327(9) 0.0287(2) Uani 1 1 d . .
O1 O 0.53078(13) 0.19317(10) 0.83089(8) 0.0216(2) Uani 1 1 d . .
O4 O -0.00592(14) -0.11736(10) 0.16495(8) 0.0225(2) Uani 1 1 d . .
N1 N 0.28711(14) 0.09613(11) 0.50053(10) 0.0161(2) Uani 1 1 d . .
C5 C 0.27834(17) -0.06959(13) 0.61145(11) 0.0162(2) Uani 1 1 d . .
H5 H 0.3220 -0.0783 0.6887 0.019 Uiso 1 1 calc R U
C6 C 0.33488(17) 0.07490(13) 0.60953(11) 0.0160(2) Uani 1 1 d . .
C10 C 0.11599(17) -0.01266(13) 0.26468(11) 0.0168(2) Uani 1 1 d . .
C7 C 0.17538(17) -0.03188(13) 0.38896(11) 0.0158(2) Uani 1 1 d . .
C9 C 0.44182(18) 0.22159(13) 0.73694(12) 0.0182(2) Uani 1 1 d . .
C4 C 0.15508(17) -0.20169(13) 0.49589(11) 0.0160(2) Uani 1 1 d . .
C2 C 0.07651(18) -0.35547(13) 0.49701(11) 0.0162(2) Uani 1 1 d . .
C3 C -0.13293(18) -0.45196(13) 0.43989(11) 0.0177(2) Uani 1 1 d . .
H3 H -0.2214 -0.4199 0.3998 0.021 Uiso 1 1 calc R U
C8 C 0.10361(17) -0.18036(13) 0.38204(11) 0.0163(2) Uani 1 1 d . .
H8 H 0.0223 -0.2645 0.3026 0.020 Uiso 1 1 calc R U
C1 C 0.20843(18) -0.40480(13) 0.55691(11) 0.0183(2) Uani 1 1 d . .
H1 H 0.3476 -0.3411 0.5948 0.022 Uiso 1 1 calc R U
C13 C 0.1465(2) 0.15857(15) 0.16388(13) 0.0246(3) Uani 1 1 d . .
H13A H -0.0054 0.1241 0.1415 0.030 Uiso 1 1 calc R U
H13B H 0.1975 0.1015 0.0850 0.030 Uiso 1 1 calc R U
C14 C 0.2398(2) 0.32938(15) 0.20466(13) 0.0272(3) Uani 1 1 d . .
H14A H 0.2088 0.3503 0.1292 0.041 Uiso 1 1 calc R U
H14B H 0.3893 0.3633 0.2319 0.041 Uiso 1 1 calc R U
H14C H 0.1812 0.3842 0.2790 0.041 Uiso 1 1 calc R U
C11 C 0.6257(2) 0.32686(15) 0.96128(13) 0.0297(3) Uani 1 1 d . .
H11A H 0.5227 0.3737 0.9982 0.036 Uiso 1 1 calc R U
H11B H 0.7412 0.4043 0.9510 0.036 Uiso 1 1 calc R U
C12 C 0.7034(3) 0.2696(2) 1.05354(14) 0.0389(4) Uani 1 1 d . .
H12A H 0.8058 0.2241 1.0162 0.058 Uiso 1 1 calc R U
H12B H 0.5878 0.1928 1.0626 0.058 Uiso 1 1 calc R U
H12C H 0.7666 0.3550 1.1411 0.058 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -6 0.0286 -0.0027 0.0051 -6.0053 0.9115 -0.0820 0.2064
0 0 6 0.0266 0.0027 -0.0051 6.0053 -0.9115 0.0820 -0.2064
-4 0 0 0.0518 -4.0003 -0.0046 0.0079 0.0353 -0.9233 0.2893
4 0 0 0.0518 4.0003 0.0046 -0.0079 -0.0353 0.9233 -0.2893
-4 5 -1 0.0661 -4.0041 4.9928 -0.9949 -0.0104 -0.8930 -0.5474
3 0 -5 0.0410 2.9979 0.0077 -5.0104 0.7331 0.6241 -0.0450
4 -4 1 0.0528 4.0034 -3.9935 0.9945 -0.0291 0.9018 0.3732
-2 1 6 0.0338 -1.9981 0.9919 6.0089 -0.9334 -0.3708 -0.2360
-2 -2 7 0.0450 -1.9956 -2.0068 7.0109 -0.9667 -0.3836 0.2523
2 -1 -6 0.0290 1.9981 -0.9919 -6.0089 0.9334 0.3708 0.2360
-4 -1 -1 0.0498 -4.0001 -1.0030 -0.9926 0.2268 -0.9458 0.4980
-3 -2 3 0.0455 -2.9975 -2.0046 3.0094 -0.3502 -0.6691 0.4622
-4 2 3 0.0427 -4.0002 1.9915 3.0098 -0.4995 -0.8647 -0.1623
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C10 O3 C13 114.81(9) .
C9 O1 C11 115.46(9) .
C6 N1 C7 116.26(10) .
C6 C5 H5 120.4 .
C6 C5 C4 119.20(10) .
C4 C5 H5 120.4 .
N1 C6 C5 123.95(11) .
N1 C6 C9 115.10(10) .
C5 C6 C9 120.78(10) .
O3 C10 C7 112.66(10) .
O4 C10 O3 124.48(10) .
O4 C10 C7 122.85(10) .
N1 C7 C10 117.89(10) .
N1 C7 C8 124.26(10) .
C8 C7 C10 117.80(10) .
O2 C9 O1 124.31(11) .
O2 C9 C6 124.13(11) .
O1 C9 C6 111.55(9) .
C5 C4 C2 121.06(10) .
C8 C4 C5 117.10(10) .
C8 C4 C2 121.79(10) .
C3 C2 C4 119.89(10) .
C1 C2 C4 120.53(10) .
C1 C2 C3 119.57(11) .
C2 C3 H3 120.0 .
C1 C3 C2 120.06(11) 2_546
C1 C3 H3 120.0 2_546
C7 C8 C4 119.12(10) .
C7 C8 H8 120.4 .
C4 C8 H8 120.4 .
C2 C1 H1 119.8 .
C3 C1 C2 120.37(11) 2_546
C3 C1 H1 119.8 2_546
O3 C13 H13A 110.2 .
O3 C13 H13B 110.2 .
O3 C13 C14 107.51(10) .
H13A C13 H13B 108.5 .
C14 C13 H13A 110.2 .
C14 C13 H13B 110.2 .
C13 C14 H14A 109.5 .
C13 C14 H14B 109.5 .
C13 C14 H14C 109.5 .
H14A C14 H14B 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
O1 C11 H11A 110.3 .
O1 C11 H11B 110.3 .
O1 C11 C12 107.18(11) .
H11A C11 H11B 108.5 .
C12 C11 H11A 110.3 .
C12 C11 H11B 110.3 .
C11 C12 H12A 109.5 .
C11 C12 H12B 109.5 .
C11 C12 H12C 109.5 .
H12A C12 H12B 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C10 1.3311(14) .
O3 C13 1.4583(14) .
O2 C9 1.2013(15) .
O1 C9 1.3389(14) .
O1 C11 1.4553(15) .
O4 C10 1.2092(14) .
N1 C6 1.3378(15) .
N1 C7 1.3392(15) .
C5 H5 0.9300 .
C5 C6 1.3901(16) .
C5 C4 1.3984(16) .
C6 C9 1.5040(16) .
C10 C7 1.5049(16) .
C7 C8 1.3873(16) .
C4 C2 1.4757(15) .
C4 C8 1.3950(16) .
C2 C3 1.4012(16) .
C2 C1 1.3984(16) .
C3 H3 0.9300 .
C8 H8 0.9300 .
C1 C3 1.3860(16) 2_546
C1 H1 0.9300 .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 C14 1.4960(17) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.495(2) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
